Photoshop
Just tried the "Snap" found under the view tab and after snap is checked make sure snap to (guides and Document bounds) are checked. A lot easier to line up shapes with each other.
Illustrator is similar but the lines don't show up to show when you are lined up.
Illustrator should show lines when you're lined up. Ctrl+U (show/hide). I think it's called smart guides.
I also use ctrl+H often (show/hide outline boundaries)... and ctrl+Y (toggle outline mode).
I guess if I had to do a clean install, one of the most important things would be the roland cut/perf cut swatches and the roland colour swatches.
I also have templates for the roland at fixed widths and graphic styles, so that I don't need to enter the page width, or waste time applying colours and the such.
I just go to the graphic styles palette, choose "cut" style (which you have to create urself), and start creating the artwork.
Same goes for print dialog - create a preset for your roland or whatever you use, so that your colour and flattener settings are always the same. (the only thing you will need to adjust for every job, is the page size, which is only one click from the dropdown menu).